7 Writing Lessons I Learned the Hard Way

If you avoid these 7 mistakes, you're on your way to a great story

It’s 1:47AM and I’m staring at my laptop. The word count on my fiction book draft ticks over 100,000 words.

I should celebrate. But instead I go back to page one and start to read. I’m somewhat horrified. Mistake here, mistake there, mistakes everywhere. I take a breath and shut my laptop.

The next day I start compiling those mistakes into a big ‘NEED TO FIX’ list.

I’ll spare you the entire list. But I pulled out seven themes of writing mistakes that are holding back that story. Hopefully, they save you the pain of making similar mistakes.

7 Writing Lessons I Learned the Hard Way

Mistake 1: Winging structure

Humans gravitate to structure. Subconsciously, we need it.

Yet I wrote this draft without a coherent structure. A big goal of the next draft is to focus on following the 4-Act Structure pretty tightly.

Here are some other structures to keep in mind — helpful for both fiction and non-fiction writing:

Reply “structure” if you’re interested in deeper dives into things like Dan Harmon’s Story Circle, 4-Act Structure, Heroine’s Journey, and other storytelling structures.

Mistake 2: Forgetting open loops

Your writing asks questions. Those questions form “Loops” in the mind of your reader. Implicitly, you’re promising to answer those questions later in the story.

  • Here, you know there are 7 mistakes. But you won’t know the 7th until you get down to the bottom. That’s a loop. This works with short-form non-fiction writing (like this newsletter!) or fiction.

Make sure to always have one open. But don’t forget to close them, either. One trick I like:

Keep a journal next to you and write down whenever you open a new loop. Then, just make sure you close them before the end of your story or edit them out later on.

Mistake 3: Losing sight of rhythm

The best stories have a flow to them. They feel unrehearsed, poetic. But that’s often because the writer took time to look at every sentence, every paragraph, and how they weave together.

I don’t have much more to say on, because this idea from Gary Provost says it perfectly:

Make It Sing

Mistake 4: Worrying about grammar

“The object of fiction isn’t grammatical correctness but to make the reader welcome and then tell a story.” — Stephen King

I spent too much time making sure my sentences had perfect grammar. Then, on re-read, I realized I should just delete entire chunks of the story. It’s better that way, but I can’t help but think about the time lost.

Lesson: Don’t worry too much about grammar until your final few drafts of something.

Mistake 5: Not capturing enough ideas

The truth (that I often don’t like) is that the majority of my ideas for a story, essay, tweet, and really anything else are bad. Even within a story,

Ed Sheeran says, “Your mind is like a dirty tap.” What he means is the first flow of your ideas comes out dirty. Then, after a while, the ideas become cleaner. Finally, after longer, they become like the water gurgling down streams in Alaska. Crisp and clear.

Julian Shapiro calls this the ‘Creativity Faucet.’ One of my favorite essays.

Mistake 6: Giving context before the hook

Have you heard someone say, “The first 50 pages were slow, but then the book got a lot better”? I’ve said it, and I bet you have too.

Here’s the thing. You and I have Attention Spans but we also have Consideration Spans.

So, as writers and storytellers, what do we do about this? You maximize impact of the Consideration Span. I think this varies by medium. If you’re on Twitter, it’s insanely short. You get a line, maybe two, to hook me. But if you’re writing a book, you get a few chapters. And most mediums fall somewhere in-between.

Cut the fluff. And if the fluff’s needed, move it to later in the story. Ask yourself, “What’s the minimum amount of context my audience needs to connect with this story?”

Mistake 7: Not separating writing and editing

You cannot be the Critic and the Creator at the same time.

When I’m writing well, there’s almost no analytical thinking going on. Just vibes. Pure flow. But any distraction, and I lose that flow as quickly as it comes.

Here’s what’s working for me:

  • No editing a first draft

  • Warming up with 5 min of copywork

  • Drinking buckets of coffee (this is key)

  • Blocking socials on both my phone and laptop

  • Not using the backspace button until a draft is written

I’m reminded of this idea from Terry Pratchett, "The first draft is just you telling yourself the story."

Have an awesome weekend,


PS: Shortform, non-fiction storytelling is one of the most powerful mediums in the world.

  • Essays

  • Memos

  • Newsletters

  • Social Posts

  • YouTube scripts

This style of Storytelling is how you package and share your ideas every single day. On Feb 5th, I’m launching Storytelling, Zero to One: a limited-time course that trains you in the 5 key skills, frameworks, and techniques you need to turn your ideas into compelling stories. Verify your interest by clicking here.

PPS: I changed the name of the course from Digital Storytelling to Storytelling, Zero to One. Just feels better. What do ya think?

A Sentence I Wish I Wrote — Trivia

What novel does this line come from?

"There’s something disturbing about recalling a warm memory and feeling utterly cold."

Login or Subscribe to participate in polls.

Want to go deeper on storytelling? 3 ways I can help:

1. If you want a practical way to improve your storywriting in less than 25 minutes daily, check out StoryWork (350+ students).

2. To get ahead of the AI curve, check out 90-Minute Novel Outline. It’s a 90-minute mini-course digging into writing fiction with AI. Prompts, processes, and more. We had 180+ students in the live session and it was awesome.

3. If you’re interested in starting or taking your newsletter to the next level, check out my Newsletter Crash Course (60+ students).

Thanks for reading! Reply any time.